Permanent waving of hair and analogous processes



United States Patent 3,142,623 PERMANENT WAVING OF HAIR AND ANALOGOUS PROCESSES Charles Zviak, Franconville, and Jean Rouet, Le Blanc- Mesnil, France, assignors to Societe Anonyme dite: LOreal, Paris, France, a corporation of France No Drawing. Filed Nov. 22, 1961, Ser. No. 154,334 Claims priority, application France Nov. 15, 1961 Claims. (Cl. 16787.1)

This invention relates to the so-called permanent waving of hair and more generally to the deformation of hair to a desired configuration.

Processes for deformation of hair which operate at room temperature, e.g. cold permanent waving, generally involve two successive operations, first a softening of the hair, which is effected by reducing the disulphide bonds of the keratin, the hair being brought to the desired configuration in the course of this softening, and secondly a hardening of the hair so that it is so in the desired configuration.

The second operation, i.e. the setting operation, involves careful and highly skilled work since the operator is working with hair saturated with a reducing liquid and wound on a curler.

In the known processes for the cold permanent de formation of hair, that is to say, without external application of heat, various reducing products have been proposed for the first operation, but in fact only reducing compounds which are mercapto compounds have had any substantial commercial success.

The setting operation can be carried out by oxidation, which simply reforms the disulphide bond, or by alkylation of the thiol groupings. The alkylation is preferably carried out with the aid of bifunctional compounds in order to restore the cross linkages. Many alkylation products have been proposed, including monoe or dihalogenated hydrocarbons, monoor dialdehydes, olefinic derivatives such as acrylic ester or maleic acid derivatives, thiosulphuric esters and derivatives comprising two quaternary ammonium functions.

It has been proposed to include such compounds in permanent waving liquids containing a reducing agent, in order to effect the reduction and the setting in one operation. However, these so-called self-neutralising liquids, as hitherto proposed, have either contained reducing agents other than thiols, or have involved the use of techniques, such as heating under a hood and excessively long periods of application, which make it impossible to achieve the rapidity and simplicity which are desirable in the practical performance of cold permanent waving.

It is an object of the present invention to provide a new single-stage process for the cold permanent deformation of hair which meets the requirements for rapidity and simplicity in the practice of cold waving, and at the same time permits the use of a reducing agent having a mercaptan function. In addition, it gives a very lasting wave of outstanding quality.

According to the present invention there is provided a process for the permanent deformation of hair which comprises constraining the hair to a desired configuration, impregnating it at room temperature with a freshly prepared aqueous composition containing a thiol reducing agent of the general Formula I:

HS--CH -R in which R denotes a group imparting to the molecule of thiol a pK for the function SH equal to or higher than 9.5, and a glycol dimethacrylate of the general Formula II:

0Hz=0-0 o(o Groom) ,.0C o-O=OH,

H3 H3 (II) where n is an integer 1 to 7 and thereafter rinsing the hair.

3,142,623 Patented July 28, 1964 and the pH of this composition is adjusted to between 7 and 9, preferably 7.5 to 8.5, the hair is left in contact with the aforesaid composition for a time, preferably between 10 and 60 minutes and rinsed. The locks of hair, which will usually be on curlers m-ay be unwound 0ptionally after a period of rest.

According toa further feature of. the invention there is provided a composition for use in the permanent deformation of hair, which comprises a reducing agent of the general Formula I set forth above, and a glycol dimethacryl ate of general Formula II. More particularly the invention provides compositions \as aforesaid in which the said substances are in an aqueous medium and the pH of the composition is from 7 to 9.

The pH of the composition according to the invention may be adjusted by the addition of an alkaline substance such as ammonia, an organic amine or an alkali salt of a weak acid.

The compositions according to the invention may in addition contain any of the adjuvants known per se for inclusion in permanent waving compositions, for example, wetting agents.

The following examples will serve to illustrate the inven- Each lock of the hair wound on curlers is carefully impregnated with the resultant solution and left in contact therewith for 30 minutes under a hood. After ample rinsing, the hair is allowed to stand for 5 minutes and the locks are unwound. The hair is then combed and adjusted to a desired hair-style and the hair is then dried. A fine permanent wave of outstanding quality is obtained.

Example 2 cc. of a solution having the following composition:

Percent Thioglycolic acid 10 Ammonia 3.5 Ammonium bicarbonate 10 Water 76.5

is mixed with 20 cc. of an emulsion having the following composition:

Percent Diethylene glycol dirnethacrylate 35 Tween 80 (wetting agent) 25 Water 40 Each lock of the hair Wound on curlers is carefully impregnated with the resultant solution and left in contact therewith for 30 minutes under a hood. After ample rinsing, the hair is allowed to stand for minutes and the locks are unwound. The hair is then combed and adjusted to a desired hair-style and the hair is then dried. A fine permanent wave of outstanding quality is obtained.

Example 3 80 cc. of a solution having the following composition:

Percent T hiolactic acid 11 Ammonia 3.5 Ammonium bicarbonate 105 Water 75 is mixed with 20 cc. of an emulsion having the following composition:

Percent Tetraethylene glycol dimethacrylate 40 Tween 25 Water 35 CH =('LCO(OCHzCH2)uOC O-(|J=CH2 CH3 CH4 in which n is an integer from 1 to 7 at a pH of 7 to 9, and thereafter rinsing the hair.

2. A process according to claim 1 wherein the glycol dimethacrylate is ethylene glycol dimethacrylate.

3. A process according to claim 1 wherein the glycol dimethacrylate is diethylene glycol dimethacrylate.

4. A process according to claim 1 wherein the glycol dimethacrylate is tetra-ethylene glycol dimethacrylate.

5. A process according to claim 1 wherein the pH of the composition is adjusted by adding thereto an alkaline substance selected from the group consisting of ammonia, an organic amine and an alkali salt of a weak acid.

6. A process according to claim 1 wherein the said composition is left in contact with the hair for 10 to minutes.

7. A composition for use in the permanent deformation of live hair which comprises a thiol selected from the group consisting of thiolglycolic acid, u-mercapto propionic acid, B-mercapto propionic acid and a mercaptoethanol, and a glycol dimethacrylate of the formula:

References Cited in the tile of this patent UNITED STATES PATENTS Cohen June 16, 1953 OTHER REFERENCES Sagarin, Cosmetics; Science, and Technology, published by Interscience Publishers, Inc., New York, 1957, pp.

. 608620 and 823-824, especially relied upon.

Chemical Abstracts, vol. 54, entry 14760g, 1960 (citing Aso, J. Polymer Sci., vol. 39, pp. 475-486). 

7. A COMPOSITION FOR USE IN THE PERMANENT DEFORMATION OF LIVE HAIR WHICH COMPRISES A THIOL SELECTED FROM THE GROUP CONSISTING OF THIOLGLYCOLIC ACID, A-MERCAPTO PROPIONIC ACID, B-MERCAPTO PROPIONIC ACID AND A MERCAPTOETHANOL, AND A GLYCOL DIMETHACRYLATE OF THE FORMULA: 